155155-64-9

Basic information

• Product Name: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE
• Synonyms: Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester;Methyl (Phenyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate Neu5Ac[1Me,4789Ac]-SPh;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetylneuraminic acid methyl ester;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester;N-Acetyl-2-phenylthioneuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate;METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE;METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-S-PHENYL-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSYLONATE
• CAS NO: 155155-64-9
• Molecular Formula: C₂₆H₃₃NO₁₂S
• Molecular Weight: 583.6
• Product Categories: Biochemistry;Sialic Acids;Sugars;Thioglycosides
• Mol File: 155155-64-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 670.995oC at 760 mmHg
• Flash Point: 359.605oC
• Appearance: /
• Density: 1.329g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -121 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: soluble in Chloroform
• PKA: 13.79±0.70(Predicted)
• CAS DataBase Reference: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(155155-64-9)
• EPA Substance Registry System: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(155155-64-9)

Safety Data

• Hazardous Substances Data: 155155-64-9(Hazardous Substances Data)

Usage

Uses

Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate (CAS# 155155-64-9) is a useful building block used in the preparation of ganglioside GM3 analogs.

InChI:InChI=1/C26H33NO12S/c1-14(28)27-22-20(36-16(3)30)12-26(25(33)34-6,40-19-10-8-7-9-11-19)39-24(22)23(38-18(5)32)21(37-17(4)31)13-35-15(2)29/h7-11,20-24H,12-13H2,1-6H3,(H,27,28)/t20-,21+,22+,23+,24+,26?/m0/s1

Upstream product

• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 108-98-5 thiophenol 
• 108740-39-2 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 59367-09-8 methyl acetochloroneuraminate 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 20298-34-4 methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-acetamido-α-D-glycero-D-galacto-2-nonulopyranosonate 
• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 934591-76-1 methyl (phenyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate 
• 1612769-03-5 methyl (phenyl 3,5-dideoxy-2-thio-4,7,8,9-tetra-O-trifluoroacetyl-5-trifluoroacetamido-D-glycero-β-D-galacto-nonulopyranosid)onate 

Relevant articles and documents

Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation

The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and α-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group

Approaches to intramolecular sialylation 2. * Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl t